Playing hookey dates back as an early Americanism from around 1848. As it fell into common usage dictionaries like Bartlett's Dictionary of Americanisms gives this example from Mark Twain's Tom Sawyer: He moped to school gloomy and sad, and took his flogging, along with Joe Harper, for playing hookey the day before. As Segnbora-t mentions, the word became extended to 'skipping work or something else one needs to do.' Harry Truman used it in Dear Bess"I played hookey from the Appropriations Committee this morning." Robert Hendrickson in Encyclopedia of Word and Phrase Origins defines the source of playing hooky as "associated with going fishing that it may even owe its life to ‘getting off the hook’ the way a fish can; anyway, school is often insufferable as a hook to schoolchildren and many kids squirming in their seats all day look like they are on a hook." Throughout teaching this never happened to me. All of my students adored school, and were heartbroken when, occasionally, an especially fine Spring day would cruelly rob them of the opportunity to watch filmstrips on, "Issues In Genetic Engineering" in college prep biology class. Truant would be a good synomym, however, it wasn't until the 19th century when compulsory attendance laws in the United States became the rule in public schools, that schoolchildren began using play hooky to mean 'skip school.'

The phrase has a number of variants. In Boston during the 19th century, one was said to be hooking jack. By 1848 playing hooky was in common use in New York City. Another colloquialism for "dishonest or underhanded" was hooky crooky derived from "by hook or by crook," meaning "by any means or tactic, fair or foul." It occurred in British print as far back as 1380 and is still common today. Experts are unsure as to what the hook and crook were. One writes:

One theory is that while tenants on English manors were not allowed to cut trees for firewood, the lord of the manor permitted them to have all the branches they could pull down with a shepherd's crook or a curved knife on a pole called a "hook."

Another lexicographer dismisses the verb hook as the origin and its euphemistic usage from the phrase hook it which dates from the 14th century means 'to escape, run away, make off", and originally meant "depart, proceed." Neither does it come from "to steal" since the Random House Dictionary of American Slang points out that the term hook it wasn't used in the United States until after 1848. Instead he thinks the term may have come the Dutch term hoekje (spelen) 'hide-and-seek'. The word hoek means 'corner' in Dutch. In 17th century New Amsterdam boys played this game around the corners of the street. Hide and seek was played by different rules back then, the players had to search for a hidden object. Hence he reasons, play hooky originally referred to the game of hide and seek.